I took a similar trajectory to most of you, like a cross between ElephantShell's and blackjaw's. I'm probably exactly in the middle of you guys, age-wise.
Melodic hardcore, like Avail, probably helped. I got into the Weakerthans through Propagandhi, which really softened my hard skull. Pedro the Lion is probably my first emo band, and it took some time because emo was a seriously bad word in the early 2000s if you were into punk. The golden age stuff was being called indie, and the MTV-aired stuff was now emo. AFI started wearing black lace shirts and the little preppy boys got lip piercings and black shirts to try to scoop girls -- the whole thing felt like a fucking invasion. There are probably still bands that I'm put off by to this day, bands I think a lot of people here revere.
Anyway, I got into indie in a big way because the punk scene started getting really fucking macho -- exactly what it used to rebel against. At the end of high school, 2003, I was a huge Modest Mouse fan. Side-by-side, I was listening to the golden age emo stuff that I considered to be classic indie: Texas is the Reason, American Football (through Owen), The Promise Ring. I swung back to punk a while later when indie took the same route punk did in the 90s, and got back into emo a few years ago from a super unlikely friend from work who, as it turns out, might be the biggest Mineral fan around.
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As for the SN record, the lyrics are what are hitting hardest for me. When I was 16, a friend in our circle shot himself with no warning sign other than the same motiveless malignance that we were all up to at the time. Nobody really talked about his death much. That summer was a strange mess.
I'm 32 now, as many years removed as I was old at the time. I had this record on at the gym and had to stop to take out my earbuds and fake a strained stretch because my eyes had welled up to blindness with tears. It's been a while since I've thought about him, and that makes me feel a little worse.